Synthesis of dipyroromethanes in water and investigation of electronic and steric effects in efficiency of olefin epoxidation by sodium periodate catalyzed by manganese tetraaryl and trans disubstituted porphyrin complexes

Condensation of pyrrole with various aldehydes in the presence of BF3 center dot etherate as an acid catalyst in water provides good yield of some dipyrromethanes. Prolongation of the reaction time with aldehydes substituted by electron-donating (mesityl) or electron-withdrawing (2,6-dichlorophenyl) groups on the ortho positions of the phenyl did not lead to decomposition or scrambling. Manganese trans disubstituted porphyrin complexes which derive from various dipyrromethanes and manganese tetraaryl porphyrin complexes including various substituents with different steric and electronic properties show good catalytic activity in epoxidation of alkenes by NaIO4 in the presence of imidazole (ImH). The study of steric and electronic effects of the catalysts on the epoxidation of olefins shows that Mn-porphyrin complexes with more bulky and electron-releasing groups on meso phenyls could increase the epoxidation yield of most alkenes.